What makes Anguilla's beaches the best in the world? White, powdery sand that stretches for miles, pristine waters and the laid-back, welcoming attitude of the Anguillan people. Swim and sunbathe all day—and all year round—at romantic public beaches like the aptly-named Rendezvous Bay, then dance to calypso music at Anguilla's annual summer festival.

The festive city of San Juan is the perfect place to experience true Puerto Rican culture. Get to know its roots by exploring the vibrant neighborhood of El Viejo San Juan (Old San Juan), which consists mostly of Spanish colonial buildings. Flesh out your self-guided history lesson with a visit to El Castillo San Felipe del Morro, a 16th century citadel that’s a UNESCO World Heritage Site. Then reward yourself with a cooling dip at Luquillo or Carolina Beach, then a tasty tour of the Bacardi rum plant.

Home to palm-lined beaches, tranquil coral reefs, and several top-tier hotels, it’s no wonder why Bavaro is one of the Dominican Republic’s most popular destinations. This resort hub combines convenience and Caribbean culture with an impressive range of activities across its expansive coastline.

U.S. citizens still need to jump through a few hoops to visit Cuba, but as visitors from around the world know, this island offers some amazing opportunities for cultural exchange. Havana is a mix of old-world architecture and of-the-moment culture. Head out of the capital city to the small town of Trinidad to see more Spanish colonial architecture. It’s a UNESCO World Heritage Site and a fantastic home base for a visit to the Valley of the Sugar Mills, a pocket of land that formerly served as the center of Cuba’s sugar industry.

The legendary Hamptons, a cluster of wealthy enclaves on Long Island’s South Fork, remains a celebrity summer playground, with splashy restaurants and nightclubs galore. But lovely beaches, fishing and kayaking attract off-the-A-list visitors, as well. Old money oozes throughout Southampton, while new wealth reigns in East Hampton. Montauk is a hit with fishermen and surfers. The Long Island Railroad travels the Hamptons in an hour. The Sag Harbor Whaling Museum and Montauk lighthouse are popular stops.

Shaped by the currents and curves of the Wisconsin River, Wisconsin Dells has been a favorite family vacation destination for more than 150 years. An explosion of indoor water parks has turned the Dells from a summer hot spot to a year-round destination. Kids will enjoy the seemingly endless supply of fun and games, from go-karts to miniature golf, sideshows to thrill rides. If the weather's right, you can take a Duck tour of land and water, and top it all off with a heaping helping of the local fudge.

As a well-known destination for both spring breakers and A-list travelers in need of a getaway, Cabo San Lucas has definite vacation cred. The beaches here range in temperament, from the serene waters of the Sea of Cortez and Playa del Amor to the kickin’ waves of Zippers, a surfing paradise. If you care to romp with locals, head to the coves and rock formations of the Cannery beaches. Kids will have a blast communing with the local animals by swimming with dolphins or taking a camel ride through the Desert Park Natural Reserve.

Soak up the sun on the well-maintained beaches of Agadir, southern Morocco's most-visited city. Palm-lined boulevards and beachfront bars add a decidedly Western-resort feel, amplified by the large number of Europeans who flock here in the winter months. It’s all about laid-back relaxation in Agadir, so ride a camel, rent a beach buggy, check out the Suq al-Had market or take the 20-minute walk up to the ruins of the Agadir Kasbah for expansive city views if you’re taking a break from the beach.

Topnotch golf courses, art galleries and seals share the dramatic oceanside landscape of La Jolla, an affluent community 15 minutes from downtown San Diego. Swimmers, snorkelers and kayakers dip into La Jolla Cove, where the protected waters shield an abundance of bright orange Garibaldi fish and sea caves indent the cliffs. The Museum of Contemporary Art San Diego, the family-friendly Birch Aquarium and the acclaimed La Jolla Playhouse deliver breaks from the sun.

A summer holiday in Villasimius offers relaxing beaches and wild nightlife. Soak up the sun by day… then club-hop till dawn. In the off-season, though, there’s a calmer vibe—and the mild weather is perfect for exploring nearby cities like Cagliari.